(5S,E)-tert-butyl 5-benzyl-3-(1-hydroxy-3-methylbutylidene)-2,4-dioxopyrrolidine-1-carboxylate

ID: ALA4549755

PubChem CID: 155550812

Max Phase: Preclinical

Molecular Formula: C21H27NO5

Molecular Weight: 373.45

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)C/C(O)=C1/C(=O)[C@H](Cc2ccccc2)N(C(=O)OC(C)(C)C)C1=O

Standard InChI:  InChI=1S/C21H27NO5/c1-13(2)11-16(23)17-18(24)15(12-14-9-7-6-8-10-14)22(19(17)25)20(26)27-21(3,4)5/h6-10,13,15,23H,11-12H2,1-5H3/b17-16+/t15-/m0/s1

Standard InChI Key:  GITBLIOWSNDYJO-MWWIPNPYSA-N

Molfile:  

 
     RDKit          2D

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   39.9474  -26.0924    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.7646  -26.0924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.0190  -25.3157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.3560  -24.8335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.6973  -25.3157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.4662  -26.7529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.9200  -25.0635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.3548  -24.0163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   41.7965  -25.0642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.2442  -26.7541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   42.4030  -25.6119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.9675  -24.2651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.7497  -24.2642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.7976  -27.4998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.6536  -26.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.1724  -27.3269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3598  -27.2404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5038  -28.0739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7559  -28.0321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.3586  -23.7180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1889  -22.9194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4109  -22.6666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8024  -23.2184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9753  -24.0150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.1806  -25.3604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.7871  -25.9081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.3516  -24.5613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  1  1  0
  1  6  1  0
  5  7  1  1
  4  8  2  0
  3  9  2  0
  2 10  2  0
  9 11  1  0
  9 12  1  0
  7 13  1  0
  6 14  2  0
  6 15  1  0
 15 16  1  0
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 16 18  1  0
 16 19  1  0
 13 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 13  1  0
 11 25  1  0
 25 26  1  0
 25 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4549755

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 373.45

Molecular Weight (Monoisotopic): 373.1889

AlogP: 3.80

#Rotatable Bonds: 4

Polar Surface Area: 83.91

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.95

CX Basic pKa: ┄

CX LogP: 4.19

CX LogD: 1.77

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.49

Np Likeness Score: 0.37

References

1. de Souza AS, Pacheco BDC, Pinheiro S, Muri EMF, Dias LRS, Lima CHS, Garrett R, de Moraes MBM, de Souza BEG, Puzer L..  (2019)  3-Acyltetramic acids as a novel class of inhibitors for human kallikreins 5 and 7.,  29  (9): [PMID:30833107] [10.1016/j.bmcl.2019.02.031]

Source

Source(1):

• Scientific Literature